If you're in search of an off-duty but also stylish look, wear a navy barn jacket with a crew-neck sweater. Does this outfit feel all-too-classic? Invite a pair of black canvas low top sneakers to mix things up a bit. If you're looking for an easy-to-transition outfit, this just might be it. This combo should erase any doubts you had about wearing casual clothes as a man in his 30s.